(RS)-3-(3-methoxyisoxazol-5-yl)butanol | 69488-85-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (RS)-3-(3-methoxyisoxazol-5-yl)butanol
• 英文别名: (RS)-3-(3-Methoxyisoxazol-5-yl)-butanol-1；3-(3-methoxy-isoxazol-5-yl)-butan-1-ol；3-(3-Methoxy-1,2-oxazol-5-yl)butan-1-ol
• CAS: 69488-85-3
• 化学式: C₈H₁₃NO₃
• 分子量: 171.196
• InChiKey: YDQCKYMVQTYRKB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  55.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (RS)-3-(3-methoxyisoxazol-5-yl)butanol 、 4-甲氧基氯苄 在 sodium hydride 作用下， 生成 (RS)-3-methoxy-5-<4-(4-methoxybenzyloxy)-2-butyl>isoxazole
  参考文献：
  名称：

  Muscarinic agonists. Syntheses and structure—activity relationships of bicyclic isoxazole ester bioisosteres of norarecoline

  摘要：

  (RS)-3-Methoxy-8-methyl-5,6,7,8-tetrahydra-4H-isoxazolo[4,5-c]azepine (O,8-di-Me-THAO, 2c) and (RS)-8-methyl-3- propargyloxy-5,6,7,8-tetrahydro-4H-isoxazolo[4,5-c]azepine (8-Me-O-propargyl-THAO, 2d) have been synthesized and evaluated as muscarinic receptor ligands in receptor binding assays and in in vitro functional assays. The corresponding compounds without methyl groups at C-8, ie O-Me THAO (2a) and O-propargyl-THAO (2b), have previously been shown to exhibit muscarinic agonistic profiles with very little discrimination between M(1)- and M(2)-receptor sites. Based on functional assays, 2c and 2d were found to be less efficacious than 2a and 2b, respectively, and 2d proved to be an M(1)-selective partial agonist. The-affinity and M(1) efficacy of 2c and 2d were comparable to those of the corresponding six-membered ring analogues, (RS)-3-methoxy-7-methyl-4,5,6,7-tetrahydro-isoxazolo[4,5-c]pyridine (O,7-di-Me-THPO, 1c) and (RS)-7-methyl-3-propargyloxy-4,5,6,7-tetrahydroisoxazolo[4,5-c]pyridine (7-Me-O-propargyl-THPO, 1d). However, neither compound 1c nor compound 1d-displayed M(1) selectivity. In summary, within this class of bicyclic muscaninic agonists, replacement of 3-methoxy by 3-propargyloxy groups generally increases muscarinic affinity without effecting the efficacy at M(1) receptors significantly. Introduction of a methyl group into the saturated ring, at the position alpha to the C-5 of the isoxazole ring (alpha-position) lead to compounds exerting lower efficacy and, in the case of compound 2d, an increased selectivity with respect to M(1) agonism.

  DOI：

  10.1016/0223-5234(96)88234-1
• 作为产物：
  描述：

  3-(3-甲氧基-5-异噁唑)丙酸 生成 (RS)-3-(3-methoxyisoxazol-5-yl)butanol
  参考文献：
  名称：

  Krogsgaard-Larsen; Larsen; Thyssen, Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1978, vol. B32, # 7, p. 469 - 477

  摘要：

  DOI：

文献信息

• Krogsgaard-Larsen; Larsen; Thyssen, Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1978, vol. B32, # 7, p. 469 - 477
  作者：Krogsgaard-Larsen、Larsen、Thyssen

  DOI：——

  日期：——
• Muscarinic agonists. Syntheses and structure—activity relationships of bicyclic isoxazole ester bioisosteres of norarecoline
  作者：S.M. Lenz、E Meier、H Pedersen、K Frederiksen、K.P. Bøgesø、P Krogsgaard-Larsen

  DOI：10.1016/0223-5234(96)88234-1

  日期：1995.1

  (RS)-3-Methoxy-8-methyl-5,6,7,8-tetrahydra-4H-isoxazolo[4,5-c]azepine (O,8-di-Me-THAO, 2c) and (RS)-8-methyl-3- propargyloxy-5,6,7,8-tetrahydro-4H-isoxazolo[4,5-c]azepine (8-Me-O-propargyl-THAO, 2d) have been synthesized and evaluated as muscarinic receptor ligands in receptor binding assays and in in vitro functional assays. The corresponding compounds without methyl groups at C-8, ie O-Me THAO (2a) and O-propargyl-THAO (2b), have previously been shown to exhibit muscarinic agonistic profiles with very little discrimination between M(1)- and M(2)-receptor sites. Based on functional assays, 2c and 2d were found to be less efficacious than 2a and 2b, respectively, and 2d proved to be an M(1)-selective partial agonist. The-affinity and M(1) efficacy of 2c and 2d were comparable to those of the corresponding six-membered ring analogues, (RS)-3-methoxy-7-methyl-4,5,6,7-tetrahydro-isoxazolo[4,5-c]pyridine (O,7-di-Me-THPO, 1c) and (RS)-7-methyl-3-propargyloxy-4,5,6,7-tetrahydroisoxazolo[4,5-c]pyridine (7-Me-O-propargyl-THPO, 1d). However, neither compound 1c nor compound 1d-displayed M(1) selectivity. In summary, within this class of bicyclic muscaninic agonists, replacement of 3-methoxy by 3-propargyloxy groups generally increases muscarinic affinity without effecting the efficacy at M(1) receptors significantly. Introduction of a methyl group into the saturated ring, at the position alpha to the C-5 of the isoxazole ring (alpha-position) lead to compounds exerting lower efficacy and, in the case of compound 2d, an increased selectivity with respect to M(1) agonism.